Portland, Maine, US.

Why now?

A waterfront town par excellence, Portland sums up what the American East Coast truly means; lobster and oysters by the bucketful followed by long walks (in this case along the Eastern Promenade), the sea breeze on your face and a picturesque lighthouse in the distance. Once you’ve had enough crisp air, cosy up in a cheap and cheerful waterfront pub with a pint.

Don’t miss

Make the most of Portland by spending as much time as possible drinking in the salty surroundings. Amble between rows of red-brick houses in the Old Port, pop between old-fashioned shops and L.L. Bean and watch wooden sailboats float by the fishing wharves. If you’re lucky enough to snag a boat ride yourself, jet over to Peaks Island for an afternoon. Drizzly days are great for visiting the Roux & Cyr International Fine Art Gallery.

Eventide Oyster Co. is a bright and airy space that’s brimming with same-day catches for lunch and dinner. Book in here for a buzzy Saturday evening spent sampling cold-water Belon oysters and fresh-as-can-be Maine lobster – either whole or in a brioche roll.

An autumnal American pilgrimage also wouldn’t be complete without some sweet treats – and we’re not talking about pumpkin-spice lattes. Check out The Holy Donut for potato delights in flavours ranging from maple bacon to toasted coconut with ginger glaze. For an all-American excursion worthy of Grease and Riverdale, make a pit stop at Beal’s Old-Fashioned Ice Cream.

Who to take with you

A sailor at heart.

When to go

The autumnal months are perfect for catching the vibrant colours of the northeast while avoiding peak summer season.

Most likely to bump into

Doppelgängers of Gossip Girl’s Nate Archibald.

Essentials to bring with you

Button-ups and Fair Isle everything – this is the place to go preppy or go home.

How to get there

Cruise into Portland International Jetport just two miles from downtown.

Discover More...

Destination Inspiration: Odessa, Ukraine

You May Also Like

City Guides

You know how you have that one incredible friend who knows their city inside out? That’s us. We take the world’s most dynamic destinations, hand-pick the best bits and give them to you in one place. This is the kind of guide that you don’t need to run by a local – it was written by one. Eat your heart out, shop until you drop, drink like a fish, dance your socks off, sleep – then repeat.


Curate your bookcase with the full SUITCASE library. From Volume 2 through 29, we've been around the world, explored uncharted landscapes and reexamined travel perceptions along the way. We invite you to do the same; grow your collection today.

Download Suitcase App
Learn More